WO2021080339A1 - Nouveau composé et diode électroluminescente organique l'utilisant - Google Patents

Nouveau composé et diode électroluminescente organique l'utilisant Download PDF

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WO2021080339A1
WO2021080339A1 PCT/KR2020/014471 KR2020014471W WO2021080339A1 WO 2021080339 A1 WO2021080339 A1 WO 2021080339A1 KR 2020014471 W KR2020014471 W KR 2020014471W WO 2021080339 A1 WO2021080339 A1 WO 2021080339A1
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compound
layer
group
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organic
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Korean (ko)
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김민준
이동훈
서상덕
김영석
오중석
심재훈
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주식회사 엘지화학
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Priority claimed from KR1020200137038A external-priority patent/KR102545206B1/ko
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Priority to CN202080013712.0A priority Critical patent/CN113423706B/zh
Publication of WO2021080339A1 publication Critical patent/WO2021080339A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material.
  • An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An organic light-emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layered structure made of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1):
  • L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene,
  • Ar 1 , Ar 2 and Ar 3 are different,
  • Ar 1 is substituted or unsubstituted C 10-60 polycyclic aryl
  • Ar 2 is a substituted or unsubstituted C 5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
  • Ar 3 is a substituent represented by the following formula (2),
  • X is O, or S
  • R 1, R 3 , R 5 to R 7 , R 9 and R 10 is connected to Formula 1;
  • the rest are each independently hydrogen or deuterium,
  • R 2 , R 4 and R 8 are each independently hydrogen or deuterium.
  • the present invention is an organic light emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer At least one of the layers provides an organic light-emitting device including the compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device.
  • the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light emitting layer 4, a hole blocking layer 9, an electron injection and transport layer ( 5) and a cathode 6 are shown as an example of an organic light-emitting device.
  • substituted or unsubstituted refers to deuterium, halogen group, cyano group, nitro group, hydroxy group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkyl Thioxy group, arylthioxy group, alkylsulfoxy group, arylsulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine Group, heteroarylamine group, arylamine group, arylphosphine group, or unsubstituted or substituted with one or more substituents selected from the group consisting of heteroaryl containing at least one of N, O and S atoms, or as exemplified above It means
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhex
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, or a chrysenyl group, but is not limited thereto.
  • heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms.
  • heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole
  • the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group.
  • the heteroaryl among the heteroarylamines may be described above for heteroaryl.
  • the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents.
  • the heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.
  • the present invention provides a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 has 1,3,5-triazine as a core, and has a structure in which three different substituents are bonded.
  • three different substituents bonded to the core are selected from the group consisting of substituted or unsubstituted C 10-60 polycyclic aryl (Ar 1 ), substituted or unsubstituted N, O, and S.
  • An organic light-emitting device including the compound represented by Formula 1 as a constituent element of an organic layer may exhibit high efficiency and long life characteristics as a synergy effect obtained by combining the three different substituents.
  • L 1 is a single bond or phenylene.
  • Ar 1 is naphthyl, phenanthrenyl or fluoranthenyl.
  • L 2 is a single bond.
  • Ar 2 is dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.
  • X is O.
  • any one of R 1 , R 3 , R 5 , R 6 , R 7 and R 10 is connected with Formula 1;
  • the rest are each independently hydrogen.
  • R 2 , R 4 and R 8 are each independently hydrogen.
  • the compound represented by Chemical Formula 1 can be prepared by a manufacturing method as shown in Scheme 1 below.
  • the present invention provides an organic light-emitting device including the compound represented by Formula 1 above.
  • the present invention is an organic light emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the At least one of the organic material layers provides an organic light-emitting device including the compound represented by Formula 1 above.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Including the indicated compound.
  • the organic material layer may include an emission layer, and the emission layer includes a compound represented by Formula 1.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the emission layer, and an electron transport layer and an electron injection layer between the emission layer and the second electrode in addition to the emission layer as an organic material layer. It can have a structure to do.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number or a larger number of organic layers.
  • the first electrode is an anode and the second electrode is a cathode, and an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate (normal type). It may be a device.
  • the first electrode is a cathode and the second electrode is an anode, and a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. It may be a light emitting device.
  • FIGS. 1 and 2 the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
  • the compound represented by Formula 1 may be included in the hole transport layer.
  • the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron suppression layer.
  • the organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the anode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), metal oxide such as indium zinc oxide (IZO), ZnO: Combination of metals and oxides such as Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline There are the same conductive polymers, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, such as LiF/Al or LiO 2 /Al. There are multi-layered materials and the like, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material, A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable.
  • a compound represented by Formula 1 may be used, or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used, but the present invention is not limited thereto. .
  • the electron suppression layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device. It refers to the layer that plays a role in improving the value.
  • the electron-suppression layer includes an electron-blocking material, and examples of such an electron-blocking material may include a compound represented by Formula 1 or an arylamine-based organic material, but are not limited thereto.
  • the light-emitting material a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 8-hydroxy-quinoline aluminum complex (Alq 3 ) carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and benz
  • imidazole-based compounds poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material may further include a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the light-emitting layer alone contains the compound represented by the above-described formula (1) as a host;
  • the compound represented by Formula 1 may be included, and the second host may further include a compound represented by Formula 4:
  • A is a substituted or unsubstituted naphthalene ring
  • Ar 4 is substituted or unsubstituted C 6-60 aryl
  • L 3 and L 4 are each independently a single bond, or a substituted or unsubstituted C 6-60 arylene,
  • Ar 5 and Ar 6 are each independently substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C 2-60 including any one or more heteroatoms selected from the group consisting of N, O and S Heteroaryl, or adamantyl,
  • p is an integer from 0 to 9.
  • the formula 4 is represented by any one of the following formulas 4-1 to 4-3:
  • Ar 4 is phenyl, biphenylyl, or naphthyl; Ar 4 is unsubstituted or substituted with one or more tert-butyl or phenyl.
  • L 3 and L 4 are each independently a single bond, phenylene or naphthalenediyl; Each of L 3 and L 4 is independently unsubstituted or substituted with one or more phenyl.
  • Ar 5 and Ar 6 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl or Adamantyl; Ar 5 and Ar 6 are each independently unsubstituted or substituted with one or more tert-butyl or phenyl.
  • p is 0.
  • Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group
  • the styrylamine compound is substituted or unsubstituted
  • at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from
  • styrylamine styryldiamine
  • styryltriamine styryltetraamine
  • metal complex examples include an iridium complex and a platinum complex, but are not limited thereto.
  • dopant material is as follows:
  • the hole blocking layer is formed on the emission layer and is preferably provided in contact with the emission layer to improve the efficiency of the organic light-emitting device by increasing the probability of hole-electron bonding by controlling electron mobility and preventing excessive movement of holes. It means the layer that plays a role.
  • the hole-blocking layer includes a hole-blocking material, and examples of such hole-blocking materials include triazine-containing azine derivatives, triazole derivatives, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives. The compound can be used, but is not limited thereto.
  • the electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer.
  • an electron injection and transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable.
  • specific electron injection and transport materials include , but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq 3 , an organic radical compound, a hydroxyflavone-metal complex, and a triazine derivative.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metal complex compounds , Or nitrogen-containing 5-membered cyclic derivatives may be used together, but the present invention is not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • subA-1 15g, 32.8mmol
  • sub8 (10.3g, 36mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subA-1 15g, 32.8mmol
  • sub9 8.2g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subA-2 15g, 29.5mmol
  • sub10 (6.9g, 32.5mmol) were added to 300ml of THF and stirred and refluxed.
  • potassium carbonate (12.2g, 88.6mmol) was dissolved in 37ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added.
  • the reaction for 11 hours the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subA-3 15g, 28.1mmol
  • sub11 6.6g, 30.9mmol
  • potassium carbonate 11.6g, 84.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.1g, 0.3mmol
  • subA-4 15g, 28.2mmol
  • sub9 7.g, 31mmol
  • potassium carbonate 11.7g, 84.6mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.1g, 0.3mmol
  • subB-1 15g, 32.8mmol
  • sub9 8.2g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subB-2 (15g, 32.8mmol) and sub12 (8.2g, 36mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subB-4 15g, 29.5mmol
  • sub11 (6.9g, 32.5mmol) were added to 300ml of THF and stirred and refluxed.
  • potassium carbonate (12.2g, 88.6mmol) was dissolved in 37ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added.
  • the reaction for 8 hours the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subB-2 (15g, 32.8mmol) and sub14 (10.3g, 36mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subC-1 15g, 32.8mmol
  • sub11 7.6g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subC-2 (15g, 28.1mmol) and sub15 (7g, 30.9mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (11.6g, 84.3mmol) was dissolved in 35ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.3mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subC-1 15g, 32.8mmol
  • sub10 7.6g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subC-2 15g, 28.1mmol
  • sub16 8.9g, 30.9mmol
  • potassium carbonate 11.6g, 84.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.1g, 0.3mmol
  • subD-1 15g, 32.8mmol
  • sub11 7.6g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subD-1 15g, 32.8mmol
  • sub15 8.2g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subE-1 15g, 32.8mmol
  • sub11 7.6g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subE-1 15g, 32.8mmol
  • sub17 8.2g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subE-1 15g, 32.8mmol
  • sub10 7.6g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subE-1 15g, 32.8mmol
  • sub18 (10.3g, 36mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 11 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subE-1 15g, 32.8mmol
  • sub14 (10.3g, 36mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 10 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subF-1 15g, 32.8mmol
  • sub9 8.2g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subF-1 15g, 32.8mmol
  • sub11 7.6g, 36mmol
  • potassium carbonate 13.6g, 98.3mmol
  • bis(tri-tert-butylphosphine)palladium(0) 0.2g, 0.3mmol
  • subF-1 15g, 32.8mmol
  • sub19 (10.3g, 36mmol) were added to 300ml of THF and stirred and refluxed.
  • potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added.
  • the reaction for 9 hours it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • subF-1 15g, 32.8mmol
  • sub14 (10.3g, 36mmol) were added to 300ml of THF and stirred and refluxed. Thereafter, potassium carbonate (13.6g, 98.3mmol) was dissolved in 41ml of water, and after sufficiently stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 ⁇ , but the following compound A-1 was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ⁇ .
  • the following EB-1 compound having a thickness of 150 ⁇ was vacuum deposited on the hole transport layer to form an electron suppressing layer.
  • the following compound 1 and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition film to form a red light emitting layer having a thickness of 400 ⁇ .
  • a hole blocking layer was formed by vacuum vapor deposition of the following HB-1 compound having a thickness of 30 ⁇ on the light emitting layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ . Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 1,000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 2X10 -7 ⁇ Maintaining 5X10 -6 torr, an organic light-emitting device was fabricated.
  • Organic light-emitting devices of Examples 2 to 26 were manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in the organic light-emitting device of Example 1.
  • Organic light-emitting devices of Comparative Examples 1 to 10 were manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 in the organic light-emitting device of Example 1.
  • Example 1 In the organic light-emitting device of Example 1, instead of Compound 1, the first host and the second host described in Table 2 were vacuum co-deposited at a 1:1 ratio, except for this, Examples 27 to The organic light emitting device of 78 was manufactured.
  • Example 1 is a structure in which compound [EB-1] is used as an electron blocking layer and compound 1 /Dp-7 is used as a red light emitting layer.
  • compound [EB-1] is used as an electron blocking layer
  • compound 1 /Dp-7 is used as a red light emitting layer.
  • an organic light-emitting device was manufactured using C-1 to C-10 instead of Compound 1.
  • the results in Table 2 show the results of co-depositing two types of hosts. When the first host and the second host are used in a 1:1 ratio, the results are better than the results of using only the first host. As the amount of holes increased as the second host was used, it was confirmed that electrons and holes in the red light emitting layer maintained a more stable balance, and the efficiency and lifespan increased a lot.
  • the compound of the present invention when used as a host of a red emission layer, the driving voltage, luminous efficiency, and lifetime characteristics of the organic light emitting device can be improved.
  • substrate 2 anode
  • hole transport layer 4 light emitting layer

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et une diode électroluminescente organique l'utilisant.
PCT/KR2020/014471 2019-10-22 2020-10-22 Nouveau composé et diode électroluminescente organique l'utilisant WO2021080339A1 (fr)

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KR1020200137038A KR102545206B1 (ko) 2019-10-22 2020-10-21 신규한 화합물 및 이를 이용한 유기발광 소자
KR10-2020-0137038 2020-10-21

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170101577A (ko) * 2016-02-29 2017-09-06 주식회사 엘지화학 함질소 화합물 및 이를 포함하는 유기 발광 소자
CN107827807A (zh) * 2017-10-23 2018-03-23 长春海谱润斯科技有限公司 一种含有咔唑结构的衍生物及其制备方法和有机电致发光器件
KR101857632B1 (ko) * 2018-02-02 2018-05-14 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN109134443A (zh) * 2018-09-12 2019-01-04 陕西莱特光电材料股份有限公司 一种新型有机电致发光层材料及其制备方法与应用
CN109879812A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 蒽类有机发光化合物及其制备方法和应用
WO2020116816A1 (fr) * 2018-12-06 2020-06-11 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170101577A (ko) * 2016-02-29 2017-09-06 주식회사 엘지화학 함질소 화합물 및 이를 포함하는 유기 발광 소자
CN107827807A (zh) * 2017-10-23 2018-03-23 长春海谱润斯科技有限公司 一种含有咔唑结构的衍生物及其制备方法和有机电致发光器件
KR101857632B1 (ko) * 2018-02-02 2018-05-14 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN109134443A (zh) * 2018-09-12 2019-01-04 陕西莱特光电材料股份有限公司 一种新型有机电致发光层材料及其制备方法与应用
WO2020116816A1 (fr) * 2018-12-06 2020-06-11 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit élément électrique organique
CN109879812A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 蒽类有机发光化合物及其制备方法和应用

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